| Windows SBS 2003 | Windows SBS 2008 |
| x86 (32-bit) Only | x64 (64-bit) Only |
| Setup asks technical questions and allows you to place data stores in the UI | Setup doesn't ask technical questions, if you want some, look at the answer file to enter the migration path, or make modifications to setup, making it more predictable, easier and faster. |
| Setup asks you technical questions about your router | Setup detects routers at 192.168.x.1 and 192.168.x.255 automatically |
| Windows Firewall disabled | Windows Firewall enabled and protecting the server before setup is finished |
| Can deploy as Edge NAT box, or Single-NIC | Deploy's as Single-NIC only, flexibility for any type of router (hardware or software) to be used in front of SBS. |
| DHCP can be deployed on Router or SBS server | DHCP strongly recommended on SBS server, can disable using advanced console only |
| Post Setup called "To Do" list | Post Setup called "Getting Started" List |
| Administrator account used, but encouraged to be renamed | New Administrator account created during setup, and the built-in is disabled out of the box |
| Configure E-mail and Internet Connection wizard was 27 wizard pages long | - Connect to the Internet Wizard for outbound connectivity
- Internet Address Management Wizard for inbound connectivity, which also configures domain names with participating domain name providers
- Add a Trusted Certificate Wizard for adding certs to the box
- Configure a Smart Host Wizard for outbound e-mail smarthost configuration
- Fix-My-Network wizard for continuous re-runs to reset configuration to factory defaults
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| User Templates | Renamed to "User Roles" |
| Power User can log into SBS administration snap-in with limited tasks | Standard User with administration links, gets additional links in Remote Web Workplace for management of Office Live, Connecting to the server, etc. |
| POP3 Connector was limited for SSL access, should be used for transition tool only. | POP3 Connector re-written to support SSL access to mail accounts. Continues to be a transition tool. |
| Remote Web Workplace was on/off for all users | Remote Web Workplace can be limited to be used for certain users only (all users by default). |
| Business-card web-site was a white paper solution to host on the local box | - Integration with Office Live for configuration of Business card web-site
- Integration with Office Live for hosted SharePoint
- Integration with Office Live for AdSense advertising
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| Backup was NTBackup based, support for USB disk drive and Tape | Backup is based on new VSS technology, and is much quicker, but no longer supports tape. |
| Email Reports Daily and Instant alerts from a defined list | An extensible list of alerts and daily reports |
| Security roll-up of the Server only, patch level of clients only. | Security roll-up of the server and clients. Including Firewall Status, AV status, Patch Status, Malware Status, Free Disk space and others! |
Windows Server 2003 Exchange Server 2003 Windows SharePoint Services v2 WSUS v2 | Windows Server 2008 Exchange Server 2007 SP1 Windows SharePoint Services v3 WSUS v3 |
| Remote Web Workplace shows all computers to connect to | Remote Web Workplace can show all computers, but defaults to a user |
| Self-Issued Certificate was your responsibility to distribute | Handy distribution tool provided that can be taken home on a USB/Floppy drive and installed on remote computers, or windows mobile devices |
| Single Leaf/Root Self-issued Certificate | Root Cert/Leaf Cert combination so renewing the leaf cert doesn't require redistributing the certificate package |
| No Anti Virus included | 120 day trial versions of OneCare for the Server, and Forefront Security for Exchange included. |
| Folder Redirection is entire network or no one. | You can choose which users have their "My Documents" redirected to the server |
| All files were able to be put on the server | You can filter which type of documents are not allowed on the server, such as music files, etc. |
| Support for Windows 2000 clients and higher | Support for Windows XP SP2 clients and higher |
| Windows Mobile access was always allowed | Windows Mobile access can be enabled by user, and devices can be managed through Outlook Web Access. |
| Two consoles, the Administrators console, and the Power Users console | Three consoles, the Administrators console, the administrators console with advanced links, and the MMC console with most native tool consoles already in it. |
| Single type of CAL | Lower price CALs for Standard server & users that aren't using the features in Premium |
| CALs purchased in 5/25 packs | CALs purchased in 1/5/25 packs |
| User needs to remember links | Administrator maintained Vista Gadget for common company links |